Syncing...How do you do it?

I posted a topic a few days ago and I think I missed the mark, maybe it was the title(@RosemaryOrchard maybe you should take it down?)

I have dropbox and I have iCloud 2TB. I have a 2017 MacBook, 2017 MacBook Pro, 2015 iMac 5K, iPad, iPhone.

I am really having trouble trying to keep everything in sync. I love the podcast and admittedly only found it about 6 months ago, I really love tech, Macs, and think of myself as tech savvy. I am now really looking/thinking into how I use my devices and how I have been wasting a lot of potential with how I use my devices together. My businesses are online and I am always on my computer. MacPowerUsers has taught me so much already…I run and now I am running more so I can listen to all the previous episodes!

Ok, back to my question. Do you guys have any tips or tricks to keeping your files/apps organized between your machines/ios devices? I just started using Hazel and am enjoying figuring it out. I am just frustrated when I use my MacBook when I travel and I am missing something that is on my iMac etc

Thanks for reading that small novel!

1 Like

For me, everything lives either in Dropbox or in a syncing solution built into a particular program (as with Bear, Ulysses, etc.). Since all of my content lives in places that sync automatically, it’s always in sync across devices.

The only exception is code, which lives in git and on Github. With that, I do occasionally end up in situations where I haven’t committed changes or manually synced the changes up to Github, which is annoying.

I have very similar equipment and I use iCloud and sync’ing is automatic. The only exceptions are some very large video files on an external drive. I don’t sync those anywhere (no need to).

I also use a cloud service (Dropbox) for everything active. For everything that I decisively complete (and everything created before 2014 or so before I took up this workflow), it goes into sub folders of a folder that I sync using Chronosync and a USB drive (my original method ca. 2004-2014). Hazel then monitors that folder and backs up anything added to a designated backup folder on Dropbox. So everything current or recently completed is in DB . And it’s all going up to Backblaze as well.

The Chronosync solution worked fine for me syncing
three Macs if you’d rather keep everything local.

After much experimentation and some frustration, I have landed on the following setup:

Files: Live in DEVONthink databases on an always-connected external 5TB hard drive. Stay in sync through their built in Dropbox integration and sync setup. Available on iOS through the DEVONthink to go app and the Files app.

Media: lives on another 5TB external drive, organized in folders and syncing using Plex Media Server. iOS Plex app.

Notes and Writing: writing files all live in Ulysses, synced via iCloud, notes in Notes app, also iCloud.

Contacts, Calendars, Photos all sync through iCloud as well.

I have found that files and documents are better via Dropbox and information is better handled through iCloud.

Paying for both services is cheap and makes syncing frustration free because they give lots of space.

I use a similar set up to @bodiequirk, but without Devonthink. Files live on Dropbox in a folder structure that works for me. What I loosely term “App Content” (eg, Ulysses, Photos, Notes) is handled by the app using iCloud wherever possible. I use a mix of iCloud (personal) and Gmail calendars (to share with non-Apple family members).

I would like to go all-in with iCloud but can’t see how I’d make the switch unless Apple introduces selective sync. I like to control what is stored locally on my device.


I live with two Macs as well (MacBook most of the day and an iMac when working from home) plus my wife’s MacBook for our small business. Dropbox has been my go to solution to make sure we both have access to all of the documents we need. As a side note, I recently had to up my iCloud storage to the 2Tb plan to accommodate my family’s storage needs but I wish I had a way to just go all in on iCloud to make sure my wife has access to all the work things but keep the kids out of the work stuff. This would keep me from paying for two different cloud services but it is what it is for now.

My ~/Documents folder is almost completely empty. I treat ~/Dropbox as my primary file storage.

If anything escapes that and I"m out and about, I can do a cloud restore from Backblaze, but that’s very rare, less than once per year.

Depending on what kind of projects you’re working on in Git, you can sync a Git repo in Dropbox. I do it all the time. The only time it gets a little weird is if you’re developing something that has thousands of tiny files. That .nodemodules directory will take approximately forever to sync.

1 Like
  • My files live in icloud, so do my pictures.

  • My documents are archived in Devonthink and

  • my files and pictures on my synology NAS.

  • An encrypted backup goes to Synology C2 cloud storage in Germany.

  • App data is in dropbox (less and less) or icloud (preference)

I’m phasing out dropbox as much as I can.
For now iCloud is my main cloud service.
And that is enough for me for now as I’ve tried to get back to using as many stock apps as I can. Just for the sake of integration.